$960,000
2 Beds
2 Baths
6,696 sqft (on 0.55 acres)
508 & 512 E Winchester Ave, Middlesboro, KY 40965
Est. Mortgage $5,746/mo*
Get Pre-QualifiedHome Highlights
Multi-Family
Built in 1980
0.55 acre lot
$143/sqft
12 Parking Spaces
Local Information
- Map ViewExplore the area around 508 & 512 E Winchester Ave.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to acquire substantial rental inventory in one convenient location. Built for efficiency and scale, each building offers significant square footage ideal for multiple residential units, making them well-suited for investors seeking strong cash flow potential in the Middlesboro market. The generous lot sizes allow for ample parking, green space, or future expansion opportunities. Situated along Winchester Avenue, the properties benefit from convenient access to local amenities, major thoroughfares, and the broader Middlesboro community. Whether you're an experienced multifamily investor or looking to expand your portfolio, this paired offering represents a solid foundation for long-term rental income and value appreciation.
Last check for updates: about 10 hours ago
Listing courtesy of Beth Combs, (606) 269-1807
Turn Key Realty
Source: Imagine MLS, MLS#26007224
Also Listed on Imagine MLS.
Home Details for 508 & 512 E Winchester Ave
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Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 6696 Square Feet |
Appliances & Utilities Laundry: Electric Dryer Hookup,Washer Hookup |
Heating & Cooling Heating: ElectricHas CoolingAir Conditioning: ElectricHas HeatingHeating Fuel: Electric |
Levels, Entrance, & Accessibility Number of Stories: 2 |
Security Security: Fire Sprinkler System |
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Exterior Home Features Roof: Shingle |
Parking & Garage Parking Spaces: 12 |
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Days on Market: 154 |
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Year Built Year Built: 1980 |
Property Type / Style Property Type: Residential IncomeProperty Subtype: Multi Family |
Property Information Parcel Number: 0694206012.00 069.42.06.011.00 |
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Price List Price: $960,000Price Per Sqft: $143 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: Active |
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Direction & Address City: MiddlesboroCommunity: City Limits |
School Information High School: Middlesboro IndHigh School District: Bell County - 87 |
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Listing Agent Listing ID: 26007224 |
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Building Area Building Area: 6696 Square Feet |
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Lot Area: 0.55 acres |
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Listing Terms: Cash, Conventional |
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Mls Number: 26007224 |
Around this home
What Locals Say about Middlesboro
At least 43 Trulia users voted on each feature.
93 % Say car is needed
87 % Say yards are well-kept
81 % Say parking is easy
77 % Say there's holiday spirit
71 % Say kids play outside
69 % Say it's dog friendly
61 % Say they plan to stay for at least 5 years
58 % Say there's wildlife
54 % Say neighbors are friendly
52 % Say people would walk alone at night
49 % Say it's quiet
44 % Say there are sidewalks
40 % Say it's walkable to restaurants
37 % Say streets are well-lit
28 % Say there are community events
27 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
Market trends in Middlesboro
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
49
2MoM
Home Value
Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Multi-Family Home | $167,000 | 10/01/25 | 2 | 2 | 1,608 | |
0.54 | Multi-Family Home | $2,750,000 | 06/01/26 | 99 | 58 | 50,352 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.04 | $116,100 | 3 | 2 | 2,100 | Off Market | |
0.05 | $108,300 | 2 | 1 | 948 | Off Market | |
0.05 | $190,100 | 3 | 2 | 1,670 | Off Market | |
0.05 | $140,000 | 3 | 1 | 905 | Off Market | |
0.05 | $106,300 | 3 | 1 | 1,100 | Off Market | |
0.12 | $120,000 | - | - | - | Recently Sold | |
0.14 | $133,900 | 3 | 2 | 1,870 | Off Market | |
0.17 | $311,200 | 4 | 2.5 | 3,054 | Off Market | |
0.17 | $275,000 | - | - | - | For Sale | |
0.15 | $182,000 | 2 | 2 | 1,608 | For Sale | |
0.17 | $65,000 | 4 | 2 | 2,592 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Apr 7, 2026 Source: Imagine MLS #26007224 | Listed For Sale | $960,000 |
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Beth Combs, Turn Key Realty
Agent Phone: (606) 269-1807
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
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Frequently asked questions about 508 & 512 E Winchester Ave
- What is the estimated monthly payment for 508 & 512 E Winchester Ave?Based on a $960,000 list price with 20% down at today's rates, the estimated monthly payment for 508 & 512 E Winchester Ave in Middlesboro, KY is approximately $5,751 (about $5,084 principal & interest, $592 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Middlesboro?Residents describe Middlesboro, KY as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See homes for sale in Middlesboro, KY.
- What are the closest schools to 508 & 512 E Winchester Ave?The closest schools to 508 & 512 E Winchester Ave in Middlesboro, KY are Middlesboro Elementary School (Pre-K, rated 5/10), Middlesboro High School (rated 6/10), Middlesboro Middle School (Elementary, rated 5/10).
- Does 508 & 512 E Winchester Ave have air conditioning?Yes, 508 & 512 E Winchester Ave in Middlesboro, KY has air conditioning.
- Does 508 & 512 E Winchester Ave have laundry facilities?Yes, 508 & 512 E Winchester Ave in Middlesboro, KY has laundry facilities.
- Does 508 & 512 E Winchester Ave have parking?Yes, 508 & 512 E Winchester Ave in Middlesboro, KY has on-site parking.
508 & 512 E Winchester Ave, Middlesboro, KY 40965 is a 2 bedroom, 2 bathroom, 6,696 sqft multi-family built in 1980. This property is currently available for sale and was listed by Imagine MLS on Apr 7, 2026. The MLS # for this home is MLS# 26007224.